FR2812869A1 - Preparation of purified hydrofluoroalkane involves subjecting hydrofluoroalkane containing (chloro)fluoro olefin impurities to purification treatment - Google Patents

Preparation of purified hydrofluoroalkane involves subjecting hydrofluoroalkane containing (chloro)fluoro olefin impurities to purification treatment Download PDF

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Publication number
FR2812869A1
FR2812869A1 FR0010546A FR0010546A FR2812869A1 FR 2812869 A1 FR2812869 A1 FR 2812869A1 FR 0010546 A FR0010546 A FR 0010546A FR 0010546 A FR0010546 A FR 0010546A FR 2812869 A1 FR2812869 A1 FR 2812869A1
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reaction
oxygen
impurities
pentafluorobutane
organic impurities
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FR0010546A
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French (fr)
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Vincent Wilmet
Arnold B M Lambert
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Solvay SA
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Solvay SA
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Priority to FR0010546A priority Critical patent/FR2812869A1/en
Priority claimed from AU2001293792A external-priority patent/AU2001293792B2/en
Publication of FR2812869A1 publication Critical patent/FR2812869A1/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00Acyclic saturated compounds containing halogen atoms
    • C07C19/08Acyclic saturated compounds containing halogen atoms containing fluorine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/383Separation; Purification; Stabilisation; Use of additives by distillation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/383Separation; Purification; Stabilisation; Use of additives by distillation
    • C07C17/386Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/389Separation; Purification; Stabilisation; Use of additives by adsorption on solids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/395Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound

Abstract

Process for obtaining 1, 1, 1, 3, 3-pentafluorobutane purified of organic impurities, according to which the 1, 1, 1, 3, 3-3-pentafluorobutane containing organic impurities is subjected to at least one purification treatment chosen from (a) extractive distillation (b) adsorption on a solid adsorbent (c) a reaction with an oxygen-containing compound and (d) a gas phase reaction with a reagent capable of reacting with at least part organic impurities, except for a reaction of elemental chlorine with unsaturated impurities under irradiation with UV light with a wavelength of at least 280 nm.

Description

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The present invention relates to a process for obtaining purified 1,1,1,3,3-pentafluorobutane.

1,1,1,3,3-Pentafluorobutane can be used as a substitute for (hydro) chlorofluoroalkanes, for example as a blowing agent, as a refrigerant or as a solvent.

1,1,1,3,3-pentafluorobutane is typically produced by reacting a chlorinated or chlorofluorinated precursor with hydrogen fluoride. The hydrofluoroalkane containing organic impurities obtained in this reaction often contains impurities such as unconverted reagents, hydrogen chloride and olefinic impurities, in particular chlorofluorinated olefins containing 3 or 4 carbon atoms. Patent application WO-A-00/14040 describes a process for the purification of 1,1,1,3,3-pentafluorobutane. According to this known process, it is possible to reduce the content of fluortrichlorethylene in 1,1,1,3,3-pentafluorobutane by ionic chlorination in the presence of FeCl3, by hydrogenation in the presence of Pd / Rh on activated carbon or in particular by reaction with fluorine.

It was nevertheless desirable to have an alternative process for purifying 1,1,1,3,3-pentafluorobutane which allows an effective reduction of the content of olefinic impurities and more particularly in olefinic impurities containing 3 or 4 carbon atoms while using technical means of easy implementation.

The invention therefore relates to a process for obtaining 1,1,1,3,3-pentafluorobutane purified of organic impurities, according to which the 1,1,1,3,3-pentafluorobutane containing organic impurities is subjected to at least one purification treatment chosen from (a) an extractive distillation (b) an adsorption on a solid adsorbent (c) a reaction with an oxygen-containing compound and (d) a reaction in the gas phase with a reagent capable reacting with at least some of the organic impurities, except for a reaction of elemental chlorine with unsaturated impurities under irradiation with light W with a wavelength of at least 280 nm.

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 It was surprisingly found that the process according to the invention allows an effective reduction of the content of organic impurities in 1,1,1,3,3-pentafluorobutane. 1,1,1,3,3-Pentafluorobutane has, under the process conditions according to the invention, physical and chemical stability. The method according to the invention can be easily implemented.

Organic impurities, the content of which can be reduced by the process according to the invention generally comprise 3 or 4 carbon atoms. These are in particular fluorinated (chloro) olefins containing 3 or 4 carbon atoms such as isomers of monochlorotrifluorobutene. Often the olefinic impurities consist essentially of such chlorofluorinated olefins containing 3 or 4 carbon atoms. In a first variant of the process according to the invention, the purification treatment is an extractive distillation. Extractive distillation is carried out in the presence of at least one extractant which is generally chosen from (hydro) chlorocarbons, (hydro) fluorocarbons, hydrochlorofluorocarbons, hydrocarbons, ketones, alcohols, ethers, esters, nitriles , hydrogen chloride and carbon dioxide.

Hydrofluoroalkanes which can be used as extractants are chosen, for example, from difluormethane, 1,1,1,2-tetrafluoroethane, 1,1,1-trifluoroethane, pentafluoroethane, 1,1,1,2,3, 3,3-heptafluoropropane and 1,1,1,3,3-pentafluoropropane.

 Other usable extractants are chosen, for example, from dichloromethane, perchlorethylene, n-pentane, n-hexane, methanol, ethanol, isopropanol, diethyl ether, aceton, 2- butanone, ethyl acetate and acetonitrile.

Preferably, the extractant is chosen from 1,1,1,3,3-pentachlorobutane, 1,1-dichloro-1,3,3-trifluorobutane, 1,3-dichloro-1,1,3- trifluorobutane, 3,3-dichloro-1,1,1-trifluorobutane, 1-chloro-1,3,3,3-tetrafluorobutane and 3-chloro-1,1,3,3-tetrafluorobutane or a mixture of these extractants.

The distillation is generally carried out at a pressure and a temperature which essentially makes it possible to avoid, if necessary, the formation of azeotropes between the extradant and 1,1,1,3,3-pentafluorobutane.

Distillation can be carried out in one or more distillation columns. Preferably, only one column will be used.

The distillation columns which can be used in the process according to the invention

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 are known in themselves. It is possible to use, for example, columns with conventional trays or columns with trays of the dual-flow type or else columns with loose or structured stacking.

In a second variant of the method according to the invention, the purification treatment is an adsorption on a solid adsorbent. The solid adsorbent can be chosen, for example, from aluminas, silicas, iron oxide compounds, zeolites and active carbon. Such adsorbents are commercially available. The adsorbent is optionally activated prior to its use in the adsorption treatment. Heat treatment or treatment to increase the Lewis acidity of the solid adsorbent is well suited. The preferred solid adsorbents are those which have undergone a treatment intended to increase their Lewis acidity, for example, washing with hydrochloric acid or with nitric acid. The contact between 1,1,1,3,3-pentafluorbutane containing organic impurities and the solid adsorbent can be carried out according to different techniques. It is possible to operate in a fluidized bed, but it is generally preferred to arrange the solid adsorbent in the form of a fixed bed of particles, which is passed through by a stream of 1,1,1,3,3-pentafluorbutane containing organic impurities. This current can be liquid or gaseous. In a variant, the adsorption is carried out in the gas phase.

When the process is carried out in the gas phase, there is a contact time between the 1,1,1,3,3-pentafluorbutane containing organic impurities and the solid adsorbent of at least 1 s. Preferably, one works with a contact time greater than 2 s. Good results have been obtained with a contact time greater than or equal to approximately 3 s. In principle, one can work with a very long contact time, for example several minutes. In practice, for reasons of efficiency, one generally works with a contact time of less than 1 minute, preferably less than or equal to approximately 30 s.

When the process is carried out in the liquid phase, there is a contact time between the 1,1,1,3,3-pentafluorbutane containing organic impurities and the solid adsorbent of at least about 2 minutes. Preferably, one works with a contact time greater than about 5 minutes.

In principle, one can work with a very long contact time, for example 120 minutes. In practice, one generally works with a contact time of less than 60 minutes, preferably less than or equal to about 30 minutes.

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 When the process is carried out in a fixed bed, the contact time is defined as the ratio of the volume of the bed of adsorbent to the volume flow rate of the stream of 1,1,1,3,3-pentafluorbutane containing organic impurities. When the process is carried out in a fluidized bed, the contact time is defined as the ratio of the volume of the tank containing the solid adsorbent to the volume flow rate of the stream of 1,1,1,3,3-pentafluorbutane containing impurities organic. The solid adsorbent is used in the form of a powder of particles, the optimum particle size of which depends on the conditions under which the process is carried out. In general, a solid adsorbent is selected whose particle diameter varies from approximately 0.1 mm to 10 mm. It is preferable to work with particles of diameter less than or equal to 7 mm. Particularly preferably, particles of diameter less than or equal to 5 mm are used. Furthermore, it is preferred to use a solid adsorbent whose particles have a diameter greater than or equal to 0.5 mm. It is preferable to work with particles with a diameter greater than or equal to 1 mm. Particularly preferably, particles with a diameter greater than or equal to 2 mm are used. At the end of the process, the solid adsorbent can be regenerated by heating at moderate temperature, for example from 100 to 250 ° C., under a gas stream, for example under nitrogen, or under reduced pressure. The solid adsorbent can also be regenerated by an oxygen treatment.

In a third variant of the process according to the invention, the purification treatment is a reaction with a compound containing oxygen. It has been found that the oxygen-containing reagents react preferentially with the organic impurities present in 1,1,1,3,3-pentafluorobutane and essentially without degradation of 1,1,1,3,3-pentafluorobutane . The oxygen-containing compound may for example be an oxygenated gas, an organic or inorganic peroxide, a peroxide salt or a peracid. Specific examples of such compounds are chosen from oxygen, ozone, hydrogen peroxide, peracetic acid, potassium permanganate, sulfuric acid and sulfur trioxide.

In another aspect of the third variant of the process according to the invention, the reaction is carried out in the presence of a base and the oxygen-containing compound is an alcohol. The base may for example be an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide. The alcohol can be chosen, for example, from methanol, ethanol and isopropanol.

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 The reaction with the oxygen-containing compound can be carried out in the presence or absence of an oxygenation catalyst. Oxygenation catalysts that can be used can be chosen, for example, from compounds and in particular from complexes containing platinum, manganese or titanium.

The reaction with the oxygen-containing compound can be carried out in the gas phase or in the liquid phase. It is preferably carried out in the liquid phase. In this case, the reaction temperature is generally at most 150 C. More often the temperature is at most 120 C. Preferably the temperature is at most 100 C. The reaction temperature is generally d '' at least -20 C. More often the temperature is at least 0 C. Preferably the temperature is at least 20 C.

The reaction pressure is generally 1 to 10 bar.

In a fourth variant of the process according to the invention, the purification treatment is a reaction in the gas phase with a reagent capable of reacting with at least part of the organic impurities, with the exception of a reaction of elemental chlorine with unsaturated impurities under irradiation with UV light with a wavelength of at least 280 nm.

The reagent can, in principle, be any reagent capable of reacting in the gas phase with at least part of the organic impurities present in 1,1,1,3,3-pentafluorobutane and in particular with olefinic impurities. The reagent is advantageously chosen from chlorine, hydrogen chloride, hydrogen, hydrogen fluoride, oxygen and ozone.

In a typical example, the reaction is a catalytic hydrogenation. Catalysts which can be used in such hydrogenation are, for example, catalysts containing a group VIII metal (IUPAC, old version) optionally supported on a support such as activated carbon. Specific examples of Group VIII metals are platinum, palladium and rhodium.

The molar ratio between the reagent and the organic impurities present in 1,1,1,3,3-pentafluorbutane is generally at least 1 mol / mol. Preferably, one works with a molar ratio of at least 1.5 mol / mol. The molar ratio between the reagent and the organic impurities does not generally exceed 1000 mol / mol. It is preferable that this molar ratio does not exceed 10 mol / mol. In the process according to the invention, a molar ratio between the reactant and the olefinic impurities of at most 3 is often maintained.

The temperature of the reaction in the gas phase is generally at least

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 minus 50 C. Preferably this temperature is at least 100 C. More preferably, this temperature is at least 150 C. Generally the temperature of the reaction in the gas phase is at most 400 C. preferably this temperature is at most 300 C. More particularly preferably, this temperature is at most 250 C. The process according to the invention applies to the purification of 1,1,1,3,3- pentafluorobutane containing olefinic impurities prepared by any synthesis process, without any prior treatment being required. The method according to the invention also applies to the purification of a 1,1,1,3,3-pentafluorobutane containing organic impurities which consists essentially of 1,1,1,3,3-pentafluorobutane and organic impurities. Typically the 1,1,1,3,3-pentafluorobutane to be purified contains at most 10% by weight of organic impurities. This content of impurities can be at most 5% by weight. It can also be at most 1% by weight. The method according to the invention can even be applied to a 1,1,1,3,3-pentafluorobutane containing at most 0.1% by weight of organic impurities.

The method according to the invention finds an interesting application in the purification of 1,1,1,3,3-pentafluorobutane obtained by hydrofluorination in particular by hydrofluorination of a chloro (fluoro) carbon.

The example which follows is intended to illustrate the present invention without however limiting its scope.

Example 1,1,1,3,3-Pentafluorobutane containing 3260 ppm of olefinic (chloro) fluorinated impurities was mixed in the liquid phase with 96% sulfuric acid in a volume ratio 1.1.1.3, 3-pentafluorobutane / sulfuric acid 1: 1. The mixture was stirred for 24 h at 40 C. After this time, the recovered 1,1,1,3,3-pentafluorobutane contained 140 ppm of olefinic (chloro) fluorinated impurities.

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Claims (16)

  1. CLAIMS 1. Process for obtaining 1,1,1,3,3-pentafluorobutane purified of organic impurities, according to which the 1,1,1,3,3-pentafluorobutane containing organic impurities is subjected to at least one treatment purification chosen from (a) extractive distillation (b) adsorption on a solid adsorbent (c) a reaction with an oxygen-containing compound and (d) a reaction in the gas phase with a reagent capable of reacting with at least part of the organic impurities, except for a reaction of elemental chlorine with unsaturated impurities under irradiation with UV light of a wavelength of at least 280 nm.
  2. 2. Method according to claim 1, in which the purification treatment is an extractive distillation.
  3. 3. Method according to claim 2 in which the extractive distillation is carried out in the presence of at least one extractant chosen from (hydro) chlorocarbons, (hydro) fluorocarbons, hydrochlorofluorocarbons, hydrocarbons, ketones, alcohols, ethers , esters, nitriles, hydrogen chloride and carbon dioxide.
  4. 4. The method of claim 3, wherein the extractant is selected from 1,1,1,3,3-pentachlorobutane, 1,1-dichloro-1,3,3-trifluorobutane, 1,3-dichloro -1,1,3-trifluorobutane, 3,3-dichloro-1,1,1-trifluorobutane, 1-chloro-1,3,3,3-tetrafluorobutane and 3-chloro-1,1,3, 3-tetrafluorobutane or a mixture of these extractants.
  5. 5. Method according to claim 1, in which the purification treatment is an adsorption on a solid adsorbent.
  6. 6. The method of claim 5, wherein the solid adsorbent is selected from aluminas, iron oxides, silicas, zeolites and activated carbon, optionally activated.
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  7.  7. The method of claim 5 or 6, wherein the adsorption is carried out in the gas phase.
  8. 8. The method of claim 1, wherein the purification treatment is a reaction with an oxygen-containing compound.
  9. 9. The method of claim 8 wherein the oxygen-containing compound is selected from oxygen, ozone, hydrogen peroxide, peracetic acid, potassium permanganate, sulfuric acid and trioxide sulfur.
  10. 10. The method of claim 8 wherein the reaction is carried out in the presence of a base and the oxygen-containing compound is an alcohol.
  11. 11. Process according to any one of claims 8 to 10, in which the reaction is carried out in the liquid phase.
  12. 12. The method of claim 1, wherein the purification treatment is a gas phase reaction with a reagent capable of reacting with at least part of the organic impurities, with the exception of a reaction of elemental chlorine with unsaturated impurities under irradiation with UV light with a wavelength of at least 280 nm.
  13. 13. The method of claim 12, wherein the reagent is selected from chlorine, hydrogen chloride, hydrogen, hydrogen fluoride, oxygen and ozone.
  14. 14. The method of claim 13 wherein the reaction is a catalytic hydrogenation.
  15. 15. Method according to any one of claims 12 to 14, in which the reaction temperature is at most 300 C.
  16. 16. Process according to any one of claims 1 to 15, in which the olefinic impurities consist essentially of chlorofluorinated olefins containing 3 or 4 carbon atoms.
FR0010546A 2000-08-10 2000-08-10 Preparation of purified hydrofluoroalkane involves subjecting hydrofluoroalkane containing (chloro)fluoro olefin impurities to purification treatment Pending FR2812869A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR0010546A FR2812869A1 (en) 2000-08-10 2000-08-10 Preparation of purified hydrofluoroalkane involves subjecting hydrofluoroalkane containing (chloro)fluoro olefin impurities to purification treatment

Applications Claiming Priority (17)

Application Number Priority Date Filing Date Title
FR0010546A FR2812869A1 (en) 2000-08-10 2000-08-10 Preparation of purified hydrofluoroalkane involves subjecting hydrofluoroalkane containing (chloro)fluoro olefin impurities to purification treatment
AU2001293792A AU2001293792B2 (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
CA 2418856 CA2418856C (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
DE60135469T DE60135469D1 (en) 2000-08-10 2001-08-10 METHOD FOR PRODUCING A CLEANED HYDROFLUOROLANE
AT01974222T AT405537T (en) 2000-08-10 2001-08-10 Method for producing a cleaned hydrofluorolane
US10/344,037 US7179949B2 (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
MXPA03001224A MXPA03001224A (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane.
AU9379201A AU9379201A (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
ES01974222T ES2312469T3 (en) 2000-08-10 2001-08-10 Process to obtain a purified hydrofluoroalcan.
PCT/EP2001/010064 WO2002012153A1 (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
JP2002517456A JP2004505936A (en) 2000-08-10 2001-08-10 Method for obtaining purified hydrofluoroalkane
CN 01817157 CN1678552B (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
EP01974222A EP1317406B2 (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
EP08104925A EP1985601A3 (en) 2000-08-10 2001-08-10 Process for obtaining a purified hydrofluoroalkane
US11/649,383 US7468467B2 (en) 2000-08-10 2007-01-03 Process for obtaining a purified hydrofluoroalkane
AU2007205746A AU2007205746B2 (en) 2000-08-10 2007-08-10 Process for obtaining a purified hydrofluoroalkane
US12/341,396 US7750195B2 (en) 2000-08-10 2008-12-22 Process for obtaining a purified hydrofluoroalkane

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2999885A (en) * 1959-09-17 1961-09-12 Du Pont Purification of fluorocarbons
WO1990008750A1 (en) * 1989-02-02 1990-08-09 E.I. Du Pont De Nemours And Company Purification of saturated halocarbons
US4950364A (en) * 1989-05-04 1990-08-21 Pennwalt Corporation Process for the separation of 1,1-dichloro-1-fluoroethane and 1,1,1,3,3-pentafluorobutane
JPH04300842A (en) * 1991-03-28 1992-10-23 Showa Denko Kk Purification of hydrochlorofluorocarbon and hydrofluorocarbon
EP0574756A1 (en) * 1992-06-13 1993-12-22 Hoechst Aktiengesellschaft Process for the removal of olefinic impurities from fluorinated C3-C6-hydrocarbons
EP0811591A1 (en) * 1996-06-06 1997-12-10 Elf Atochem S.A. Process for the purification of saturated hydrofluorocarbons
US5944962A (en) * 1995-10-03 1999-08-31 Laroche Industries, Inc. Process for photochlorination
DE19940104A1 (en) * 1998-09-03 2000-03-09 Solvay Fluor & Derivate Purification of 1,1,1,3,3-penta:fluoro-butane, used as a blowing agent for plastic foam, involves treatment with a solid inorganic sorption agent or diatomatic molecules capable of addition to multiple bonds

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2999885A (en) * 1959-09-17 1961-09-12 Du Pont Purification of fluorocarbons
WO1990008750A1 (en) * 1989-02-02 1990-08-09 E.I. Du Pont De Nemours And Company Purification of saturated halocarbons
US4950364A (en) * 1989-05-04 1990-08-21 Pennwalt Corporation Process for the separation of 1,1-dichloro-1-fluoroethane and 1,1,1,3,3-pentafluorobutane
JPH04300842A (en) * 1991-03-28 1992-10-23 Showa Denko Kk Purification of hydrochlorofluorocarbon and hydrofluorocarbon
EP0574756A1 (en) * 1992-06-13 1993-12-22 Hoechst Aktiengesellschaft Process for the removal of olefinic impurities from fluorinated C3-C6-hydrocarbons
US5944962A (en) * 1995-10-03 1999-08-31 Laroche Industries, Inc. Process for photochlorination
EP0811591A1 (en) * 1996-06-06 1997-12-10 Elf Atochem S.A. Process for the purification of saturated hydrofluorocarbons
DE19940104A1 (en) * 1998-09-03 2000-03-09 Solvay Fluor & Derivate Purification of 1,1,1,3,3-penta:fluoro-butane, used as a blowing agent for plastic foam, involves treatment with a solid inorganic sorption agent or diatomatic molecules capable of addition to multiple bonds

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* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 118, no. 19, 10 May 1993, Columbus, Ohio, US; abstract no. 191166, YOSHINAGA, MASAMI ET AL: "Purification of hydrochlorofluorocarbons and hydrofluorocarbons" XP000354050 *

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